In Pictures: The Greatest Risk Of All

What's anything worth? We asked a slew of strivers--entrepreneurs, politicians, athletes and show-business types--what they consider to have been the riskiest moves of their lives. Their answers were as diverse as their jobs, but all support the same conclusion: The best results come to those willing to take a chance--an important reminder as the U.S. economy braces for even rougher weather.

James Dyson, 61

Founder of his eponymous engineering company

(Dyson is an engineer who made his fortune designing vacuum cleaners. His estimated net worth: $1.6 billion.)

I spent about five or six years developing a completely different kind of vacuum cleaner. I built over 5,000 prototypes to get the system to work. Every year I was getting further and further into debt. In the end, I owed something like $4 million. I took out two or three mortgages on my house. If I failed, everything I owned would've gone to the bank. Everybody thought I was completely mad. [As it turned out] I repaid the bank loan within about four or five months of first selling the product. The bank kept using me in their advertising as an example of how they loan money.

--Interviewed by Matthew Kirdahy

Kai (36) and Charles Huang (38)

Co-founders of RedOctane, creator of the "Guitar Hero" videogame

Kai: The launch of "Guitar Hero" meant the survival of the company. We had been in business for six years by that time. We saved the company from bankruptcy twice; this was a third time. The biggest kick in the gut was knowing that if we couldn't raise the money, "Guitar Hero" wouldn't launch, and we didn't know what we were going to do. We finally borrowed $500,000 in the eleventh hour from a family friend. We were $2 million in debt when we launched the product.

Charles: A couple years later, somebody said to me, "Wow, I can't believe you took all your money and bet it on a plastic guitar." (Happy ending: Videogame publisher Activision later bought RedOctane for $100 million.)

--Interviewed by Matthew Kirdahy

Bill Bartmann, 59

Former CEO of Commercial Financial Services, a debt collection agency

My greatest risk was making the decision to not call any witnesses on my behalf in a trial where the U.S. federal government had indicted me on 57 felony counts, which carried a maximum [combined] penalty of 600 years in prison. Although it was the ultimate "all-in" poker hand, I was confident the 12 members of the jury would agree with my innocence. After a few nerve-wracking hours of deliberation, they unanimously acquitted me of all charges. Two years later, the government issued an apology, conceding there was "no fraud" at CFS. (Note: Bill Bartman has an estimated net worth of $100 million.)

--Interviewed by Matthew Kirdahy

Puneet Nanda, 40

CEO of Dr. Fresh, maker of oral care products

In 1992, a lot of wholesalers were coming to New Delhi to purchase simple things like toothbrushes, toothpaste and condoms. I decided that somebody needed to tackle the Russian market, so I took the risk and went. Everybody there had to pay a Mafia fee. There was no real government; these ex-KGB guys controlled everything. Still, business was very good and it was exciting. One day, a new Mafia boss came by and chopped off the hand of my office manager. Later, some men came to my home and left me badly injured. My brother flew in and took me to a hospital in Sweden. I left everything behind and returned to India. Dr. Fresh now operates out of California and is carried in 42 different countries. August was the first month we sold to Russia since I left.

--Interviewed by Lauren Streib

Kit DesLauriers, 38

The first person to ski from all Seven Summits.

We were the only team to climb Everest. There were no safety nets, no fixed lines established, freezing winds. We had to spend an unplanned night at 26,000 feet, with very little food and water. The next day, we skiied the Lhotse Face, 5,000 feet of blue ice on a 50-degree slope--by far the most intense ski descent of our lives. At one point, we ran out of oxygen. I kept telling myself: "Don't sit down and die. Just keep going." It's really easy to let your mind get a hold of you, but the journey taught me we are much more than our minds.

--Interviewed by Nicole Perlroth

Allan Cumming, 43

Actor

The greatest risk I've ever taken in my life was having unprotected sex. Luckily, nothing happened; I'm still alive and disease-free and it's nothing I'd advocate.

--Interviewed by Jane Tuv

Doug Woods, 57

Co-founder, DPR Construction

In 1989, I was working as a senior manager for a construction company when the owners informed me that they planned to bequeath the business to their family rather than their loyal management team, as they had previously led us to believe. I knew then that I had to take the leap and start a business of my own. A year later, I launched DPR with a few partners. It wasn't a great time to start a business; the first Iraq war was going on and the economy was in a downturn. There were nights I would wake up wondering, "Is this going to work? Did I make a mistake?" Two years later, we did $35 million in revenues.

--Interviewed by Melanie Lindner

Louis Hernandez, 41

CEO of Open Solutions, developer of banking software

In 1999, at the height of the dot-com boom, I turned down several offers at rapidly growing Internet companies to join the team at Open Solutions, which served a relatively slow-growth, conservatively regulated industry. I took the risk on Open Solutions because I believed it to have long-term potential, while the future of dot-coms seemed more uncertain to me. I also felt that Open Solutions had a product that could inspire and lead the financial services industry in the next generation of banking. When I started here, Open Solutions had 100 employees and $14 million in annual revenue; by 2007, those numbers were 2,000 and $500 million.

--Interviewed by Melanie Lindner

Richard Jackson, 54

CEO of Jackson Healthcare

In 2006, I decided that Jackson Healthcare should acquire a company called World Health Alternatives, a medical staffing business twice the size of my own business and trading on the Nasdaq. It was a hairy deal--the company was pulling in $300 million in annual revenue but losing $1 million per month and rapidly approaching bankruptcy; its financial documents were inaccurate, the CEO had quit after some suspicious ethical behavior and the FBI was getting involved. We paid $43 million for the company in 2006; last year, it took in $18 million on $220 million in sales. It was a huge risk--and an even bigger success.

--Interviewed by Melanie Lindner

Alan B. Miller, 71

Founder and chairman of Universal Health Services, the third-largest operator of hospitals in the U.S.

In 1982, we had a $65 million contract to buy and rebuild a rundown city hospital in McAllen, Texas. It was growing, but the market was not that developed and the previous buyers got cold feet. We only had three other little hospitals, so I felt that this was either going to establish us or I don't know what. There was more than one sweating session on this deal, I can tell you. The project turned out to be a boon for the city and our business. You bet the ranch once--you never bet it more than that. I wouldn't, anyway.

--Interviewed by Matthew Kirdahy

Heather B. Armstrong, 33

Founder of Dooce.com, a Web site about motherhood

I started my site back in 2001 to talk about pop culture and my single life in Los Angeles. I never really intended to make money with it. My husband found out the number of readers and realized that if we got advertising, it could support the family. I was very hesitant to do it. I knew that there was going to be a huge backlash in terms of readers thinking that this would change the tone or affect the irreverence that I use in my writing. [Finally] I said, "let's do it"--and it's been a huge success.

--Interviewed by Adriana Loeff

Michael Chasen, 36

Co-founder of Blackboard, an education-technology company

Matthew Pittinsky and I were working in the Higher Education Group at KPMG when we noticed a trend: Schools were spending millions to wire classrooms and dormitories to the Internet, but there was no software to make the investment useful for teaching and learning. We decided to quit our jobs and start our own company to design that software. The biggest risk was telling my fiancé one month before our wedding that I was going to quit my high-paying job to gamble on a "big idea" with my old friend and college roommate--not exactly what she had signed up for. Fortunately, she was very supportive and encouraged me to follow my dream. She also said she would still marry me. Risk averted.

Curt Westergard, 50

President, Digital Design & Imaging Service

(Note: The company uses balloons to do high-angle photography of construction sites.)

We were contracted in 2003 to capture 360-degree panoramic views from 1,376 feet to support the proposed design of Larry Silverstein’s Freedom Tower [to be built at Ground Zero]. I had never had the nerve nor opportunity to [work] at that kind of altitude before. We did not know what the air pressure and lift would be that high up. Five years of research and testing, a huge investment and my pride in this first step in rebuilding the fallen World Trade Center were all at stake. We hit our target height, and when the [balloon] landed 18 minutes later, we were relieved beyond description to see most dizzying and impressive views from the future observation deck of the Freedom Tower.

--Interviewed by Alan Farnham in 2007

Courtesy of Draper Fisher Jurvetson

Tim Draper, 48

Co-founder of Draper Fisher Jurvetson, a venture capital firm

My brother-in-law and I saw some horses up on a hill. I asked him if he had ever rode bareback. He said "no," but that he was game for anything. I hopped on one horse, and it didn’t budge, but then my brother-in-law got onto another one--it moved and he hopped off. Both horses got spooked and took off running. It must have been going 40 miles per hour. I looked down and thought, "If I jump off, I will die," and "If I hold on, I will die." I decided to hold on so that I could at least get a fun ride. The horse went about 400 yards before finally coming to an abrupt stop and almost sending me flying.

--Interviewed by Erika Brown in 2007

Courtesy of Robert Polet

Robert Polet, 52

Chief executive, Gucci Group

We were attacked by an elephant in Botswana last year. We came around a bend in the road and stumbled upon a herd with their young. It was my daughters, Anne Christine [and] Francine, and my wife, Caroline, and me with a guide/driver. To defend her baby, the mother came at us, trumpeting and throwing up a lot of dust, loudly. Instead of going in reverse, the driver went full speed right at the elephant and at the very last moment took a sharp turn around it. He swerved through bush and around trees with the elephant following for two minutes before it let us go.

--Interviewed by Sue Hoppough in 2007

Courtesy Danica McKellar

Danica McKellar, 32

Known as Winnie Cooper on the hit TV series The Wonder Years. Upcoming book, Math Doesn't Suck, targeted to middle school girls, due in August.

After my six-year run as "Winnie Cooper" ended, I was hungry to find out who I was outside of this character everyone loved so much. At the risk of being forgotten completely by the media, I went to college and pursued a passion that had nothing to do with acting: mathematics. By the end of an intense four years at UCLA, I had co-authored a new math proof (the "Chayes-McKellar-Winn" Theorem), which the media, in fact, loved. As it turned out, math itself blazed my entry back into the spotlight and consequently into wonderful acting jobs like The West Wing and others. You just never know, do you?

--Interviewed by James M. Clash in 2007

Courtesy R. J. Hillhouse

R.J. Hillhouse, 44

Author of Outsourced

A buyer for the Estonian mafia--which at the time was still just figuring things out--was on a mission in East Germany and needed funds. Finding things there with value in the West was tough--the good stuff in Eastern Europe (artwork, jewels, antiques, caviar) was all in the Soviet Union. I cut a deal where I'd lend him some money to tide him over, and go to Moscow a few weeks later to collect payment in rubles (at 100% interest--hey, he was desperate). When the time came, I headed to the mafia's club in southern Moscow. I collected my money and became a regular until one night my "Spidey sense" went off, and I left the place immediately. Days later I returned to find it closed by Soviet authorities after a shootout and murder.

--Interviewed by Mike Maiello in 2007

Courtesy Robert Anderson

Robert Anderson, 49

The biggest risk I ever took was when my relatives in Norway got me a job on my semester off working as a "stancer" at the local metal-working factory. Quick research revealed no one had ever worked as a "stancer" without losing fingers, and I was a rock climber--losing anything would ruin me. Every day I had to grit my teeth, go to work and watch my hands. I lasted six months and escaped with all 10 fingers intact. A decade later, I'd lose a toe climbing on Everest without oxygen. My fingers are still intact.

--Interviewed by James M. Clash in 2007

Courtesy Brian Binnie

Brian Binnie, 54

Piloted SpaceShipOne 69 miles above the Earth to win the $10 million Ansari X Prize

The choice between a poke in the eye or the opportunity for public speaking sends me into serious deliberation. The same adrenalin rush that serves so well in sports and other physical pursuits is my albatross on stage. So the day after flying out of the atmosphere, I was presented with one of the greatest dilemmas of my life--an invitation to appear on national TV, filmed live, under the mischief of one David Letterman. Accepting was out of the question, yet not accepting seemed an equally absurd conclusion. [Binnie accepted.]

--Interviewed by James M. Clash in 2007

Courtesy of Sarah Fisher

Sarah Fisher, 26

Holder of the fastest qualifying time for a woman at the Indy 500 (four-lap average: 229.439 mph)

The biggest risk I ever took was when I walked away from Walker Racing in 2002. They wanted me to race the Atlantic Series in preparation for the Champ Car World Series. But I firmly believed in the Indianapolis 500 and helping the IndyCar Series grow to become the premier open-wheel series. I grew up dreaming about the Indy 500, and I wanted to contribute to that. I walked away from a solid job opportunity to make it on my own. I didn't have a job waiting for me but I said, "I'll find one," and I did.

--Interviewed by James M. Clash in 2007

Courtesy of Christine Dennison

Christine Dennison, 38

Co-founder, Mad Dog Expeditions, a New York-based diving company

My greatest risk was continuing in 1997 with Mad Dog Expeditions, the diving company I had co-founded three years earlier, after my partner decided to leave. We were still struggling to establish ourselves within the fledgling adventure-dive industry, and there was, as they say, no more money in the "kitty." I lived on my credit cards for several months while refocusing the company not only to take clients on exotic adventure dives, as in the past, but to train them as well. The gamble paid off. Ten years later, it is an ongoing adventure for Mad Dog--and a profitable one.

Charlie Crist, 50

Governor of Florida

The greatest risk I ever took was running against U.S. Sen. Bob Graham in 1998. [Crist lost in a landslide.] I learned that humility is always important to bear in mind. I also learned the value of being persistent and never giving up. If I hadn't taken the risk back then and run for the U.S. Senate, I probably wouldn't be where I am today.

Doveen Schecter, 46

Founder, Dove of the East

One of the first things I had to do when I started my company was to hand-carry my product designs to a factory in China. I was armed with a 10-page nondisclosure agreement. But that just meant that if the factory owner stole my ideas, my only recourse would be a Chinese court case I couldn’t afford. In two years I have sold my products in eight countries and 28 states, but I had no idea how an expanding business would push me to keep taking further risks. Every day I take a leap of faith, both calculated and intuitive.

--Interviewed by Robyn Meredith in 2007

Courtesy of John Wood

John Wood, 43

Founder of Room to Read and author of Leaving Microsoft to Change the World

In 1999 I left a senior position at Microsoft during the height of the technology boom to start Room to Read, a charity focused on building schools and libraries in the developing world. During my travels, I met so many children in the poorest parts of the world lacking access to schools, books and libraries that I began cashing in small amounts of stock to help them. Two hundred shares of Microsoft stock was enough to build an entire school in rural Nepal. I eventually left my corporate job to follow my passion and literally bring books on the back of a yak to rural Himalayan villages. Eight years later, Room to Read has set up nearly 4,000 school libraries and put 3 million books into the hands of eager young readers.